CN-116670586-B - Sulfonic acid derivative of naphthalimide, photoacid generator comprising same and photoresist composition comprising same

Abstract

The present invention relates to a sulfonic acid derivative of naphthalimide and a photoacid generator and a photoresist composition each comprising the same, and more particularly, to a sulfonic acid derivative compound of naphthalimide having excellent absorption ability for light of i-line (365 nm) wavelength, which is very easy to prepare a polymerizable composition due to very high solubility in an organic solvent, and has excellent thermal stability and shows good acid yield, and a photoacid generator and a photoresist composition each comprising the same.

Inventors

• WU QUANLIN
• Cui Dahe
• CUI WEINA
• Li Deluo
• CUI ZHIEN
• Jiang Qidui
• JIN MINZHENG
• LI YUANZHONG
• LI ZHIWAN

Assignees

• 株式会社三养社

Dates

Publication Date

20260508

Application Date

20211228

Priority Date

20201228

Claims (9)

1. 1. A sulfonic acid derivative compound of naphthalimide represented by the following chemical formula I: [ formula I ] , In the chemical formula I, R 1 and R 2 are each independently C 1 -C 12 straight-chain alkyl or C 3 -C 12 branched-chain alkyl which is substituted or unsubstituted by one or more halogen atoms or alicyclic hydrocarbon groups, C 3 -C 12 alicyclic hydrocarbon groups which are substituted or unsubstituted by one or more halogen atoms, C 6 -C 20 aryl which is substituted or unsubstituted by one or more halogen atoms or C 1 -C 12 alkylthio groups, C 7 -C 20 aralkyl which is substituted or unsubstituted by one or more halogen atoms, or C 7 -C 20 alkylaryl which is substituted or unsubstituted by one or more halogen atoms, R 3 is C 1 -C 12 straight-chain alkyl which is substituted or unsubstituted by one or more halogen atoms or alicyclic hydrocarbon groups or C 1 -C 12 alkoxy-C 1 -C 4 alkyl which is substituted or unsubstituted by one or more halogen atoms.
2. 2. The sulfonic acid derivative compound of naphthalimide according to claim 1, wherein R 1 is methyl, ethyl, trifluoromethyl, 2-trifluoroethyl or nonafluorobutyl, R 2 is methyl, ethyl, propyl, isopropyl, butyl or cyclohexyl, and R 3 is methyl, ethyl, propyl, hexyl, heptyl, cyclohexyl, methoxyethyl or butoxyethyl.
3. 3. The sulfonic acid derivative compound of naphthalimide according to claim 1, wherein the sulfonic acid derivative compound of naphthalimide is selected from the following compounds: 。
4. 4. a photoacid generator comprising the sulfonic acid derivative compound of naphthalimide according to any one of claims 1 to 3.
5. 5. A photoresist composition comprising the sulfonic acid derivative compound of naphthalimide according to any of claims 1 to 3, and a binder resin.
6. 6. A substrate coated with the photoresist composition of claim 5.
7. 7. A patterned substrate obtained by exposing and developing the coated substrate of claim 6.
8. 8. A display device comprising the patterned substrate of claim 7.
9. 9. A semiconductor device comprising the patterned substrate of claim 7.

Description

Sulfonic acid derivative of naphthalimide, photoacid generator comprising same and photoresist composition comprising same Technical Field The present invention relates to a sulfonic acid derivative of naphthalimide and a photoacid generator and a photoresist composition comprising the same, and more particularly, to a sulfonic acid derivative compound of naphthalimide, which has an excellent absorption ability for light of i-line (365 nm) wavelength, has very high solubility in an organic solvent, is very easy to prepare a polymerizable composition, and has excellent thermal stability and exhibits good acid yield, and a photoacid generator and a photoresist composition comprising the same. Background Photoacid generators are compounds that generate acid by irradiation with light, and the acid generated by the photoacid generator breaks down a part of the composition or causes crosslinking according to the constituent components of the photoresist composition, thereby changing the polarity of the polymer in the composition. The polarity change of the polymer causes a difference in solubility to a developer between an exposed portion and an unexposed portion, and as a result, positive lithography or negative lithography can be realized. In the photoresist composition, the photoacid generator has excellent energy sensitivity (ENERGY SENSITIVITY) to the irradiated light so that a fine pattern can be formed, but there is a problem in that the sensitivity of the photoresist cannot be increased to a satisfactory degree only by using a conventional photoacid generator. Therefore, there is a need to develop a photoacid generator that has excellent photosensitivity so that sufficient sensitivity can be achieved in a small amount, thus having an effect of reducing costs, and that has excellent sensitivity so that exposure dose can be reduced, and yield can be improved. In addition, increasing the solubility of the photoacid generator in the main solvent of the photoresist has the advantage that various compositions can be easily prepared. Various developments have been made for improving the photosensitivity and improving the solubility of the naphthalimide compound. For example, a naphthalimide compound is prepared by using ultra-low temperature conditions of-70 ℃ and a metal compound such as 1-butyllithium in korean laid-open patent No. 10-2017-0125980, and a naphthalimide compound is prepared by using a bromine-substituted compound in korean laid-open patent No. 10-2017-0042726 and korean laid-open patent No. 10-2012-01111153. Disclosure of Invention Technical problem to be solved An object of the present invention is to provide a sulfonic acid derivative compound of naphthalimide which exhibits excellent photosensitivity suitable for use as a photoacid generator for photolithography, high solubility in an organic solvent, excellent thermal stability and good acid yield, a photoacid generator comprising the same, and a photoresist composition. Technical proposal In order to achieve the above object, a first aspect of the present invention provides a sulfonic acid derivative compound of naphthalimide represented by the following chemical formula I: [ formula I ] In the case of the formula I described above, R 1 and R 2 are each independently a substituted or unsubstituted aliphatic hydrocarbon group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group or a substituted or unsubstituted alkylaryl group, R 3 is independently a substituted or unsubstituted aliphatic hydrocarbon group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted alkylaryl group, or a group of formula R 4-O-(CH2)n -, wherein n is an integer from 1 to 12, and R 4 is a substituted or unsubstituted aliphatic hydrocarbon group. In a second aspect the present invention provides a photoacid generator comprising a sulfonic acid derivative compound of a naphthalimide according to the present invention. A third aspect of the present invention provides a photoresist composition comprising the naphthalene dicarboximide sulfonic acid derivative compound according to the present invention, and a binder resin. According to another aspect of the present invention, there is provided a substrate coated with the photoresist composition according to the present invention, a patterned substrate obtained by exposing and developing the coated substrate, a display device including the patterned substrate, and a semiconductor device including the patterned substrate. Advantageous effects The sulfonic acid derivative compound of naphthalimide according to the present invention has excellent solubility in a solvent for photoresist and excellent thermal stability, and is very excellent in sensitivity to light for lithography (e.g., light of i-line (365 nm) wavelength), and thus can provide a pattern having excellent developability, taper angle, pattern stability, etc. ev